Book ideas #12: Ben Macintyre reading cluster

Lessons from double agents

In a previous post, I wrote about Adolf Tolkachev, a Soviet engineer who leaked military secrets to the CIA. If stealing one country’s secrets is fraught with risks, being a double agent is even more dangerous. Despite the constant danger, some double agents have operated successfully for a long time. Their stories offer lessons about the necessary conditions for success and highlight the operational hazards of being a double agent. The portrayed double agents are Kim Philby and Oleg Gordievsky, chronicled in two excellent Ben MacIntyre books (A Spy Among Friends, The Spy and the Traitor). Philby was an MI6 officer who secretly worked for the KGB, while Gordievsky was a KGB officer who secretly worked for MI6.

Invariance explains success

Successful double agents, just like successful professionals in other domains, need to share some characteristics. When reading about a single individual in isolation, it’s easy to focus on what sets them apart. For example, Philby was a notoriously heavy drinker. He also had four wives (not simultaneously, though). Before we reach for the bottle or look up a nearby courthouse as aspiring double agents, we should pause. Gordievsky, unlike Philby, was not a heavy drinker, and his marriage counter stopped at a mere two. In other words, drinking and marriage habits are not predictive of double agent success because both men became successful despite their different habits in these realms.

Therefore, only traits that both men (and other double agents) share can explain double agent success. (But note that this is not a sufficient condition for success because unsuccessful people could also share that trait.) One of these shared traits was their ability to withstand pressure and deny accusations against them. Philby was repeatedly questioned by MI5, the counterintelligence arm of the British intelligence service. He never admitted to spying for the KGB. Similarly, Gordievsky vehemently denied the charges against him despite being drugged and pressured by the KGB. (Ironically, the advice of never confessing came from Philby, who was then living in Moscow as an outed KGB agent and imparted this lesson to prospective KGB agents.)

There can be no differences in double agents’ capacity to withstand pressure because confessing would cut their careers short (i.e., the definition of an unsuccessful agent).

You must be consistently lucky

Another important shared aspect in double agent success stories is luck. Not just casual, one-off luck but consistent luck. Here are some examples where Philby’s and Gordievsky’s careers could have gone off the rails if they had been unlucky.

Philby was a war correspondent during the Spanish Civil War. He was sitting in a car when a shell exploded close to him, killing the other war correspondents around him. You can be the most promising double agent ever, but that doesn’t mean anything if you are killed by a stray shell. In another close call, a Soviet intelligence officer, Walter Krivitsky, defected to the West. In his interview with MI5, he mentioned that Soviet intelligence had sent an English agent to assassinate Franco during the Spanish Civil War. Even though Philby was not mentioned by name, an investigation could have put him in a difficult spot. Nothing substantive came of this potentially devastating intelligence.

Gordievsky had his fair share of luck, too. The KGB didn’t arrest him when he was back in Moscow, even though they knew he was working for MI6. They wanted to catch him red-handed and were complacent about his chances of escape. Before Gordievsky, no suspected spy under KGB surveillance had ever escaped from the Soviet Union. Another incident that could have caused his downfall was his divorce from his first wife. She made assertions about Gordievsky’s duplicity and his potential status as a spy. To Gordievsky’s relief, these claims were discounted as implausible accusations by a bitter ex-spouse at the time.

Success is dangerous

Success comes with increased visibility, and spies are no exception in this regard. Naturally, spies don’t give world tours or build a large online following. But even if their identity is closely guarded, news about their existence spreads within their organization in proportion to their accolades. As more people learn about them, the probability increases that information about them will end up in the wrong hands—either by the negligence of a friend or by the deliberate acts of a mole. Let’s call this cross-sectional vulnerability.

Vulnerability can be temporal, too. Any given act is not suspicious in itself, but it becomes suspicious in light of other (later) acts. For example, Philby was a known Communist during his studies at Cambridge. In isolation, flirting with Communism could be discounted as the intellectual explorations of a young and malleable mind. It turned out his first wife was an Austrian Communist. This, too, could just be youthful indiscretion, driven by passion or lust. He also accessed personal files of British agents working in the Soviet Union, a territory outside his remit at the time.

While any one of these actions could describe a non-spy, the totality of the evidence starts hinting at double loyalties at some point.

The CIA knew about a prized MI6 double agent, but they didn’t know it was Gordievsky. They set out to identify him. The agent provided political intelligence, rather than military or technical intelligence. Knowing the structure of the KGB enabled the CIA to narrow down its search to those in a specific branch of the KGB. Another cue was that topics about England featured prominently in his reporting (Gordievsky worked at the KGB’s London office then). Further cues came from the time he worked in Denmark as a diplomat and the speed with which he secured a UK visa. Coinciding with his time in Denmark, several KGB agents operating in Scandinavia were arrested. The Danish intelligence service suspected he was a KGB man. Despite relaying this information to their British counterpart, Gordievsky’s UK visa was quickly approved, an unusual outcome for a suspected KGB spy.

Many people had their UK visas quickly approved. Similarly, many worked in England or in regions where several KGB agents were swept up in crackdowns. But there was only one person who fit all these criteria.

Accumulating all this evidence takes time: a careless drunken comment here, a checked-out confidential document there, potentially with years passing between these incidents. But the longer the double agent operates, the more circumstantial evidence he accumulates against himself. Furthermore, evidence that seems unusable at the time might become usable later. Just as technological progress enabled carbon dating, future advances in computing might make a spy’s encrypted messages decipherable years or decades later.

Build a castle on sand

Every intelligence agency wants to have access to high-ranking enemy officials. One option is to recruit someone already high-ranking. Another option is to cultivate someone while they are unimportant, hoping they will become important many years later. In both cases, the moment the agent starts working for you, you want them to stop producing real intelligence for the enemy while appearing just as productive as before.

If he were to be promoted, Gordievsky needed to generate what his KGB bosses considered useful intelligence. To accomplish that, MI6 would pass little-known public information to him that could seem confidential (called chicken feed in spy circles). They also suggested contacts he should cultivate. For example, he established contact with Conservative Party researcher (and MI5 access agent) Rosemary Spencer. She knew he was a KGB agent but was not aware that he was also working for MI6. To Gordievsky’s KGB bosses, this connection seemed like a new, promising lead.

Getting promoted in one’s organization does not depend only on performance. There also needs to be a vacancy. Or if there isn’t, it needs to be created. That’s what MI6 did. They expelled Gordievsky’s immediate bosses to open the path for him to become the KGB chief in London. Now, this can’t be done in an obvious way, lest Gordievsky come under suspicion. Most KGB agents operated under diplomatic cover, meaning they officially worked for the Soviet embassy. MI6 used this fact to their advantage. Their solution was to expel many Soviet diplomats simultaneously, making it seem like Gordievsky’s bosses were just part of a generalized crackdown.